HCID 59350344, compound → HCID 46216724, compound

HRID 2271386Notes

Reaction equation

HRID 2271386 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([S:11]([N:14]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[S:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24]C)=[C:20]([O:26]C)[CH:19]=2)(=[O:17])=[O:16])(=[O:13])=[O:12])[CH:6]=[CH:7][C:8]=1[O:9]C>C(Cl)Cl.B(Br)(Br)Br>[OH:2][C:3]1[CH:4]=[C:5]([S:11]([N:14]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[S:15]([C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([OH:26])[CH:19]=2)(=[O:17])=[O:16])(=[O:12])=[O:13])[CH:6]=[CH:7][C:8]=1[OH:9]

Participants

4

Reactant 1

HCID 59350344HCID 59350344, compound

Product 1

HCID 46216724HCID 46216724, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 25134Boron tribromideSolvent

Procedure

To a 0° C. solution of N-(3,4-dimethoxyphenylsulfonyl)-N-hexyl-3,4-dimethoxybenzenesulfonamide (0.080 g, 0.181 mmol) in 1.81 mL of CH2Cl2, boron tribromide (1.81 mL, 1M in CH2Cl2) was added dropwise under a nitrogen atmosphere. The resulting solution was allowed to stir overnight and warm to room temperature. Upon quenching with a few drops of water, a precipitate formed and was filtered. The solid was triturated with ethyl acetate and the filtrate was evaporated, affording 0.046 g (65%) of N-(3,4-dihydroxyphenylsulfonyl)-N-hexyl-3,4-dihydroxybenzenesulfonamide as white solid. 1H NMR (acetone-d6, 400 MHz) δ 7.43 (d, J=2.3 Hz, 2H), 7.34 (dd, J=2.3, 8.2 Hz, 2H), 6.97 (d, J=8.2 Hz, 2H), 3.58 (m, 2H), 1.61 (m, 2H), 1.22 (m, 6H), 0.81 (t, J=6.9 Hz, 3H); 13C NMR (acetone-d6, 100 MHz) δ 150.61, 145.17, 131.03, 121.33, 115.07, 115.06, 49.01, 31.10, 26.05, 22.30, 13.42; HRMS, ES calcd. for C18H23NO8S2Na[M+Na]+468.0763, found: 468.0755.

Workup

  1. customUpon quenching with a few drops of water
  2. customa precipitate formed
  3. filtrationwas filtered
  4. customThe solid was triturated with ethyl acetate
  5. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-208806a972124685b6fb24d78da84de7
Source dataset
uspto-grants-2015_09
Patent number
US09120744B2

Reaction notes

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